Ethanol → Ethyl 6-hydroxynaphthalene-1-carboxylate

HRID 646014Notes

Reaction equation

HRID 646014 reaction equation
S(Cl)(Cl)=O.[OH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12]([C:16]([OH:18])=[O:17])=[CH:11][CH:10]=[CH:9]2.[CH2:19](O)[CH3:20]>>[OH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:11][CH:10]=[CH:9]2

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 54638006-Hydroxy-1-naphthoic acid

Product 1

HCID 59264852Ethyl 6-hydroxynaphthalene-1-carboxylateYield 87%

Procedure

Thionyl chloride (2.3 mL, 31.9 mmol) was slowly added to a solution of 6-hydroxy-1-naphthoic acid (3 g, 15.9 mmol) in ethanol (140 mL) and stirred under N2. After addition, the reaction mixture was heated at reflux under nitrogen for 6 days. The reaction mixture was cooled to room temperature and concentrated to give the crude product as an oil. The oil was carefully partitioned between 5% NaHCO3 and EtOAc. The organic phase was separated and washed with brine, dried over MgSO4, filtered and the filtrate was concentrated to give 3 g (87%) of the product as a red amorphous solid. 1H NMR (400 MHz, DMSO-d6): δ 9.92 (s, 1 H), 8.57 (m, 1 H), 7.92 (d, J=8 Hz, 1 H), 7.85 (d, J=7 Hz, 1 H), 7.45 (t, J=8, 1 H), 7.20-7.18 (m, 2 H), 4.38-4.33 (m, 2 H), 1.34 (t, J=7 Hz, 3 H).

Workup

  1. additionAfter addition
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux under nitrogen for 6 days
  4. concentrationconcentrated
  5. customto give the crude product as an oil
  6. customThe oil was carefully partitioned between 5% NaHCO3 and EtOAc
  7. customThe organic phase was separated
  8. washwashed with brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-56707f64ffdc411f83d49fab4143c7c6
Source dataset
uspto-grants-2010_04
Patent number
US07705028B2

Reaction notes

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